A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

Hampshire County Holiday Rentals

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Top Cities in Hampshire County

Our top choices for Hampshire County holiday rentals

1. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is NZ$472
includes taxes & fees
23 Nov - 24 Nov
The Creation Station is a cozy place so make yourself at home.

2. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"Great place for a couple to stay. Hostess was fantastic. We had everything we needed. Would definitely recommend and would stay again!"
United States
Doreen R.
The price is NZ$410
includes taxes & fees
9 Nov - 10 Nov
Newly Built Barn Loft in Pioneer Valley

3. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is NZ$861
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton

4. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is NZ$872
includes taxes & fees
9 Nov - 10 Nov
Penthouse overlooking downtown Amherst!

5. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is NZ$716
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.

6. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (40 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is NZ$458
includes taxes & fees
30 Nov - 1 Dec
Serene 1-bedroom suite on 75 acre horse property

7. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is NZ$332
includes taxes & fees
9 Nov - 10 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

8. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property and host. Left a suit accidentally and they were extremely accommodating in helping us get it back."
United States
Kimberly D.
The price is NZ$2,165
includes taxes & fees
18 Nov - 19 Nov
Amherst -NEW - Campus Convenience & Social Privacy

9. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (13 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is NZ$182
includes taxes & fees
9 Nov - 10 Nov
Vacation Village in the Berkshires

11. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,261 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is NZ$195
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge

12. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is NZ$403
includes taxes & fees
9 Nov - 10 Nov
Modern Studio Ideal for Traveling Professionals

13. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is NZ$534
includes taxes & fees
9 Nov - 10 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center

14. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is NZ$420
includes taxes & fees
9 Nov - 10 Nov
Modern Studio Ideal for Traveling Professionals

15. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is NZ$427
includes taxes & fees
9 Nov - 10 Nov
Lovely 2nd Floor Apartment

16. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (18 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is NZ$738
includes taxes & fees
9 Nov - 10 Nov
Townhouse with Pool Table - Renovated w/ King Bed

17. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is NZ$611
includes taxes & fees
7 Dec - 8 Dec
Cozy Home in Holyoke with 3 bedrooms

18. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$141
includes taxes & fees
9 Nov - 10 Nov
1 King Bed|Smoking, Micfridge

19. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is NZ$407
includes taxes & fees
9 Nov - 10 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

20. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is NZ$387
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom apartment in Chicopee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hampshire County Hotel Reviews

Find out more about Hampshire County

Everything you need to know about Hampshire County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hampshire County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hampshire County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hampshire County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hampshire County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hampshire County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hampshire County holiday rentals we have selected for you start as low as NZ$182 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hampshire County rentals

At Expedia, we put the best Hampshire County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hampshire County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hampshire County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hampshire County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.